Castellina in Chianti

One of Chianti’s most charming hilltop villages, Castellina was fortified by Florence as an outpost against Siena, and for centuries its fortunes depended on who was on top in their endless war. It was lost to a combined Sienese-Aragonese siege in 1478, although after the fall of Siena itself in 1555 Florence lost interest in Castellina, and today it looks much as it did in the quattrocento: the circuit of walls is almost intact, complete with houses built into and on top of them.

The Rocca, or fortress, is in central Piazza del Comune; its mighty donjon and covered walkway, the Via delle Volte, were part of the 15th-century defensive works. Since 2006 it has been home to the Museo Archeologico del Chianti Senese with finds from around the region, including Greek black figure vases and a reconstructed, ornate Etruscan chariot found nearby at the Ipogeo Etrusco di Montecalvario, a recently restored 7th-century BC Etruscan tumulus a 10 min walk north of the center on Via Fiorentina.